Crystals of (1,5,3-dithiazepan-3-yl)-alkanoic acids with achiral and chiral amino acid moieties have been obtained, and their structures were studied using a single crystal X-ray technique. Simple crystal systems, namely monoclinic, triclinic, and orthorhombic, were revealed in a series of the studied compounds. The reference 1,5,3-dithiazepan-3-ol forms head-to-head cyclic dimeric associates R 2 2 (6) via strong O-H⋯N intermolecular hydrogen bonds. The achiral 1,5,3-dithiazepanes form head-to-head cyclic dimers R 2 2 (8) between two carboxylic groups, whereas the co-crystals involve solvent molecules to constitute dimeric pairs R 3 3 (11) and R 2 2 (8) through O⋯H and N⋯H hydrogen bonds. These dimers further contribute to the aggregation of layers and stacks due to diverse H⋯H and S⋯H contacts. The chiral dithiazepanes form head-totail R 1 2 (6), R 2 2 (7), and R 2 2 (8) cyclic dimers between the carboxylic group of one molecule and the dithiazepane moiety of the other one through H⋯H, S⋯H, and O⋯H intermolecular contacts. Hirshfeld analysis has shown that S⋯H (9.2-19.8%) and O⋯H (5.4-18.2%) intermolecular hydrogen bonds as well as weak H⋯H contacts (40.2-64.0%) are predominant in all the compounds to form crystal packing.
CrystEngCommThis journal is † Electronic supplementary information (ESI) available: Additional tables with some bonds and with crystal data and structure refinement of the studied compounds. Fig. 12 Fragments of the crystal packing of 7 with intermolecular contacts. View along the b axis.Fig. 13 Fragments of crystal packing of 8: (a and b) view along the c axis and (c) along the b axis.
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